三种丝状真菌对沙皮菌素 A、C 和 G 的生物转化。

Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi.

机构信息

Facultad de Ciencias Químicas, Instituto Multidisciplinario de Biología Vegetal (IMBIV-CONICET), Universidad Nacional de Córdoba , Casilla de Correo 495, 5000 Córdoba, Argentina.

出版信息

J Nat Prod. 2016 Jun 24;79(6):1658-67. doi: 10.1021/acs.jnatprod.6b00310. Epub 2016 Jun 10.

DOI:10.1021/acs.jnatprod.6b00310

PMID:27285201

Abstract

Incubation of salpichrolide A (1) with Rhizomucor miehei produced hydroxylation in rings B and C (C-7 and C-12) and led to C-5-C-6 epoxide opening, while incubation of salpichrolides C (2) and G (3) with R. miehei led to epoxide opening at the C-24-C-25 and C-5-C-6 positions, respectively. Biotransformation of salpichrolide A (1) with Cunninghamella elegans produced stereoselective hydroxylated, oxidized, and reduced derivatives in different positions of the A, B, and C rings and C-5-C-6 epoxide opening. In addition, selective epoxide opening at the C-5-C-6 or C-24-C-25 positions was obtained from the incubation of salpichrolide A (1) with Curvularia lunata.

摘要

与米黑根毛霉共培养时，沙皮菌素 A（1）发生 B 环和 C 环（C-7 和 C-12）的羟化，导致 C-5-C-6 环氧化物开环，而与米黑根毛霉共培养时，沙皮菌素 C（2）和 G（3）分别导致 C-24-C-25 和 C-5-C-6 位的环氧化物开环。与卷枝毛霉共生物转化沙皮菌素 A（1）可在 A、B 和 C 环以及 C-5-C-6 环氧化物的不同位置生成选择性羟基化、氧化和还原衍生物。此外，从沙皮菌素 A（1）与新月弯孢霉的共培养中获得了 C-5-C-6 或 C-24-C-25 位的选择性环氧化物开环。